What happens when life knocks you flat, your business burns you out, and your next move isn’t obvious?

Most people wait for clarity. Alan Underwood started building anyway.

In this episode, Kristi and Raphael sit down with Alan, a high-performance coach and real estate developer who went from owning restaurants to reshaping his entire life around purpose, discipline, and community-focused development. Alan talks openly about the years he spent chasing work that drained him, the moment he realized he needed a different path, and the slow climb into a career that finally aligned with who he wanted to become.

His story is raw and real: navigating the entitlement process without a roadmap, pushing through doubt, learning to take imperfect action, and discovering that the right mindset isn’t just helpful in development, it is the foundation.

This episode is for anyone who’s rebuilding, starting over, or grinding quietly toward a project that feels bigger than their current resources. Alan’s journey proves that you don’t need certainty to get moving. You just need the courage to bet on yourself.

What We Cover:

✅ How burnout from restaurant ownership pushed Alan to rethink everything

✅ The shift from chasing money to building a life with purpose

✅ Why action beats perfection in development and entrepreneurship

✅ Navigating the entitlement process without experience

✅ Alan’s community-first approach informed by personal challenges

✅ His commitment to service through Angel Flight West

✅ What’s next for his development journey and coaching work

✅ Alan’s advice to anyone trying to step into real estate development for the first time

Bold Truth:

You don’t rise to the level of your resources. You rise to the level of your grit and your willingness to act before you feel ready.

🎧 Listen now to hear how Alan trusted the process, navigated setbacks with grit, and found out that the project that changes your life is often the one you choose to start before you’re prepared.

Connect with Alan:

🌐 Website: https://thealanunderwood.com/

📲 Instagram: https://www.instagram.com/thealanunderwood/

💼 LinkedIn: https://www.linkedin.com/in/the-alan-underwood/

Listen + Subscribe:

Watch full episodes on YouTube or listen on Spotify & Apple Podcasts.

Want more from Kristi?

Hear how she’s helping locals become developers in their own communities without the gatekeeping.

🎧 Local Real Estate Developer Podcast Playlist →

👉 Ready to become a local developer in your town? Apply for the Mentorship:

https://www.localrealestatedeveloper.com/dev-mentorship

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https://linktr.ee/localrealestatedeveloper

🎬 Chapters

00:00 Introduction to the Podcast and Guests

01:26 Alan Underwood's Background and Journey

06:46 Transitioning from Restaurants to Real Estate

09:46 Lessons from Entrepreneurship and Grit

16:37 The Shift to Real Estate Development

19:43 The 100-Unit Apartment Complex Experience

25:03 Challenges in the Entitlement Process

28:48 Navigating Utility Challenges in Development

30:34 Finding Motivation Through Adversity

34:01 The Importance of Taking Action

36:59 Overcoming Analysis Paralysis in Investing

41:08 Community-Driven Development and ADUs

45:22 The Impact of Angel Flight West

52:02 Future Aspirations and Legacy Building

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